I've thought Microsoft licensing has been out of control for years. I'm a small business person. Just trying to figure out which copy of *Windows* or *Office* to buy, in their multiple guises is a nightmare.

For my money, the extra $500-$1000 spent on a Macintosh desktop and attendant OSX, and applications not only simplifies one's life, but gives one BMW-type quality in both the hardware and software. Add the FileMaker database for end-user database connections to back-end databases of all kinds including mySQL, and you have a versatile suite of productivity software which is stable, reliable and oh yes, legally licensed without having to attend three-day courses.

Microsoft is the only company whose licensing discussions literally give me headaches. Sadly Rob, I'm not surprised that came out more confused. I've found there are some third parties that understand the licensing program better than some of the people at MS.

We are taking a serious look at Google. As another reader points out, Google appears to indeed be syphoning off some of the MS business. I think we can run much of our end user business on Google enterprise apps, but dragging end users through change is not without its cost.

I teach three-day courses in Microsoft licensing and negotiations, and one of the first things I tell my classes is "you shouldn't be here." There's no way anyone should need to spend three (it's threatening to go to four) days in a classroom just to figure out how to buy a vendor's products.

Customers should never confuse their MS rep with an expert in MS licensing. They're trained to sell and they get virtually no training in licensing. I am an expert, but then this is all I do and it is a full-time job to keep up with the rules. For any other company, that's sheer overhead.

I'm also disturbed by Microsoft's complete disinterest (and I'm sure they're not alone) in helping customers out by building some kind of internal license enforcement or even notification into their software. With very few exceptions the software does not stop enterprise users from doing something they aren't licensed to do. That works in MS's favor, of course, keeping customers fearful that somewhere along the lines they overstepped the rules, so they had better toss another million onto the pile to keep the licensing police away. I'd rather see people spend their money in more useful ways, but the truth is that it is trivially easy for a system administrator to do some normal and common IT task that exposes their company to thousands of dollars in compliance penalties.

The idea that customers are supposed to know the rules is absurd, since Microsoft never announces or describes in detail some very significant changes. But understand their culture: this is probably the largest company in the world that does not license any Microsoft software. They do not feel your pain nor do they curse their staff with any requirement to know anything at all about licensing.

Exactly - time is our most valuable commodity. If I am on a call or in-person meeting with someone and they veer off track, I don't have a problem saying so, and I appreciate when people do the same for me. Better than walking away thinking "there's an hour I'll never get back."

Microsoft has basically taken a page from Oracle regarding licensing. Take Oracle's DB for instance, there are different levels of the db product and their is tiered licenses to support those levels. Solaris, once free, but charged you for certain updates, is now free for something like 60 days, but you get no access to any updates. With Oracle's DB products, not even the CPUs are free. With any Oracle products, access to updates is extremely pricy and based on an annual support contract FOR EACH PRODUCT! And then you see Larry's $100M World Cup boat and you know where your money went, because it sure wasn't on better support. At least with Microsoft, Windows and SQL Server updates don't require you to read through literally pages and pages of documents regarding how to install the patch that you so desperately need. I would bet though that Microsoft is headed directly in Oracle's direction. It really is no wonder that so many IT pros are looking at Google and open source solutions instead.

This is far more common place than it should be. As soon as you start talking about licensing the door is open for analyzing every single product you use and trying to negotiate ways to leverage the various plans. The thing that bothers me most is that Microsoft has taken to quarterly meetings with me to "keep me up to date". When I need to spend three hours with them every few months to make sure we are using our licensing plan to it's potential and that we aren't missing something there is a problem.

A while back I interviewed the SVP of ops at Jordache about their IT overhaul in concert with the brand's modernization. Much of that makeover was tied to moving everything online, and Google was the major piece. The exec contacted Microsoft first, but found pricing problematic: "it was a high level of negotiation."

McGreavy rightfully notes that Google's not for every organization and comes with its own considerations and pitfalls. But it sure seems like Google has siphoned off some corporate productivity and collaboration business from Microsoft simply by offering more straightfoward pricing.

Lorna, you ask a good question about the runaway Microsoft presentation. I could have stepped in, but how would that have looked? I'm the CIO of the company and I arranged for the session. If I can't control a simple vendor session, what message does that send? Definitely a judgement call, but effectiveness is a careful balance of executation and perception. I let the CRM thing run its course, but I was steamed!

A good way to keep vendors on track and to break thru the deliberate obfuscation is to schedule 2 or 3 vendors on the same day. Make it clear that you are talking to all three. Makeit clear to the rep and his boss that you only have money to spend on voice and video this year. Tell the rep they have two hours to address your needs, remind them every half hour how much time they have, and usher them out right on the dot. If they choose to talk about CRM when you want to hear about integrated voice and video conclude the meeting with "That was very interesting and we're looking forward to hearing what Google has to say about our problems".

Follow that up with a note to the district manager cc'ing the Head of Sales that your rep wasted two hours of your time.

As InformationWeek Government readers were busy firming up their fiscal year 2015 budgets, we asked them to rate more than 30 IT initiatives in terms of importance and current leadership focus. No surprise, among more than 30 options, security is No. 1. After that, things get less predictable.